1-beta-naphthyl-1-aminoethane salt of penicillin



Patented Get. 6, 1953 UNITED STATES PATENT OFFICE 1 -fl-NAPHTHYL-1-A1WINOETHANE SALT OF PENICILLIN Harley W. Rhodehamel, Jr., Indianapolis, Ind., assignor to Eli Lilly and Company, Indianapolis, Ind., a corporation of Indiana N Drawing. Application February 13, 1952, Serial No. 271,442

2 Claims. (Cl. 260-239.1)

This invention relates to a novel penicillin salt Example 2 ll h a f v e d is i l tl f naphthyl-l-amino- To an aqueous 9 3 of the p ethane or its salts can be combined with penl- 2 dsalt 5 1 5 m g of gat cillin or its salts by neutralization or metathetia a so u Ion 0 y cal reactions to form a sparingly soluble peniammoelthane Pydrochlonde 5 of W cmin salt thereby ffo din a means of precipi The mixture is cooled and stirred occasionally tating penicillin from solution, and of purifying whfireupon the sllghtly -I D Y penicillin. Moreover, the novel penicillin salt amlnoethane Salt of 1981110111111 G p p tate can be utilized therapeutically. A prolonged The S s Separated, a d r ed in vacuol penicillin blood level can be secured upon admin- I claim: istering the salt parenterally by methods known 1. The 1- 3-naphthyl-l-aminoethane salt of to the medical art. penicillin represented by the following formula The following examples illustrate the preparain which P represents penicillin. tion of the novel salt of this invention:

Example 1 CH3 To a solution of 2 g. of penicillin (e. g. a commercial mixture of the several penicillins) dissolved in 30 ml. of amyl acetate are added 2 g. of 1-p-naphthyl-l-aminoethane dissolved in 50 ml. of amyl acetate. The mixture is cooled and stirred occasionally whereupon the l-p-naphthyll-aminoethane salt of penicillin precipitates. T maphthyl'bammoethane salt of The salt is isolated as by decantation or filtrapemcfllm tion, and dried in vacuo. HARLEY W RHODEHAMEL' JR The salt is represented by the following formula in which P represents penicillin:

H-NHal UNITED STATES PATENTS Number Name Date 2,547,640 Goldman Apr. 3, 1951 References Cited in the file of this patent 

1. THE 1-B-NAPHTHYL-1-AMINOETHANE SALT OF PENICILLIN REPRESENTED BY THE FOLLOWING FORMULA IN WHICH P REPRESENTS PENICILLIN. 